The 7 Best Medieval Old Town Tours in Italy

1.Palermo: Medieval castles of Caccamo & Cefalù. Small Group Tour

★★★★★★★★★★5.0 · 24 reviews · 9 hours (approx.) · from $238Our pick

Spend about nine hours exploring Cefalù and Caccamo from Palermo, with hotel pickup at Hotel Politeama, a professional guide, and private air-conditioned transport. See Cefalù’s UNESCO-listed cathedral and medieval washhouse, then tour Castello di Caccamo. Guides may include Alessandra or Tatiana, and lunch is not included.

“Alessandra was an excellent guide. She made sure the tour focused on our interests. Joseph was our driver. He always made sure that we were comfortable. He made a recommendation for us to visit an olive oil manufacturer and got a personal tour. A wonderful day of making memories in Sicily.”

Check availability →Read our full review

2.Private 2-Hour Tour of the Medieval Castle over Lake Como

★★★★★★★★★★5.0 · 9 reviews · 2 hours (approx.) · from $144

Join guide Daniele for a private English-language walk through Spina Verde Regional Park to Castello Baradello. Explore its old walls and Tower of Time museum, then step onto the private terrace for broad views of Como and Lake Como. Choose a morning, sunset, or midnight visit, with wine and snacks available.

“We had a private tour with Daniele and he was wonderful! We absolutely love him and the history he told us about the area. He was very friendly and detailed which we loved. We totally recommend!”

Check availability →Read our full review

3.Private daytour medieval castles from Civitavecchia port

★★★★★★★★★★4.5 · 7 reviews

Travel privately from Civitavecchia to five unusual Italian sights: Santa Severa Castle, Abbadia Castle, the hill village of Ceri, Civita di Bagnoregio, and Orvieto. Rolando’s private Mercedes van gives your group a flexible day, but confirm the pickup point and route before booking, since some tour details also describe Pompeii, Sorrento, and Positano.

“Everything was great! Our first time in Europe and Rolando made this day tour to Pompeii and Amalfi coast amazing. Rolando picked us up at our apt rental on time. He was friendly and professional. He takes super pride of his Mercedes vaRead more”

Check availability →Read our full review

4.E-bike adventure among medieval castles and old villages

★★★★★★★★★★5.0 · 6 reviews · 4 hours (approx.) · from $137

You’ll ride an e-bike through the Veneto countryside with a small group of up to eight people. Expect vineyards, fruit trees, old villages, Ponte Visconteo, Borghetto sul Mincio, and Scalinger Castle. Guides such as Fabio and Elisabetta add local stories and help set a relaxed pace.

“The e-bikes were easy and fun to ride. The scenery was spectacular and the buildings and history very interesting. Our guide was friendly and informative. Would highly recommend this tour.”

Check availability →Read our full review

5.E-bike adventure among villages and medieval castles

★★★★★★★★★★4.5 · 4 reviews · from $101Best value

Join a small English or Italian tour from Villafranca di Verona and ride an e-bike past an 800-year-old castle, vineyards, orchards, and the Tione River to Borghetto sul Mincio. Your guide handles the route and bike briefing, with an Italian aperitif included. The four-hour ride suits active couples, friends, and solo visitors.

“My husband and I planned a weekend in Verona and wanted to try a different and dynamic experience. As luck would have it, we found a beautiful sunny day, ideal for this ride. We met our guide at the Veronaintour headquarters, punctual, precise and available for the entire activity. We prepared the e-bikes and set off to discover the area. After visiting the Castle of Villafranca di Verona, we pedaled along the Tione, in a pleasant naturalistic context. We arrived in Borghetto sul Mincio, which literally amazed us with its beauty. The village is intimate and romantic, thanks to its views and the presence of old water mills. A real…”

Check availability →Read our full review

6.From Palermo: Medieval castle tour of Caccamo and Cefalù.

★★★★★★★★★★5.0 · 4 reviews · from $225

Travel from Palermo with guide Tatiana and driver Giuseppe to seaside Cefalù and hilltop Caccamo. You’ll see Cefalù’s UNESCO-listed Duomo, medieval wash house, and shops, then tour one of Sicily’s largest Norman-era castles. Transport, guide, and castle entry are included, while lunch and sweets cost extra.

“Tatiana and Giuseppe were excellent. Great information and very attentive. Also very flexible in meeting our interests. Enjoyed the tour!”

Check availability →Read our full review

7.Montone: Medieval Dinner in Cardaneto Castle

★★★★★★★★★★5.0 · 2 reviews · 1.5 hours · from $117

At Cardaneto Castle near Montone, you’ll spend 90 minutes in a private tower room with Alessandro and the local team, tasting Umbrian and Tuscan wines alongside salumi, pecorino, handmade pasta, beef or grilled vegetables, and house-made olive oil and nocino. Free parking and a castle visit are included.

“Bellissima esperienza in tutto. Il posto curato nei dettagli, l'accoglienza e la gentilezza di Alessandro, la bontà del cibo...tutto perfetto”

Check availability →Read our full review